Get him a copy of The Game: Penetrating the Secret Society of Pickup Artists. Let him practice his "negs" on you.
I knew a guy in his mid-thirties who swears it works. He landed himself a hot university-aged girlfriend despite his overbearing mood problems. I took that as some kind of proof.
But I really am the worst person to give advice on this topic.
My own advice on women out of your league? Let them prey on you.
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Knowing that death is certain and that the time of death is uncertain, what's the most important thing?
—Bhikkhuni Pema Chödrön
Humankind cannot bear very much reality.
—From "Burnt Norton," Four Quartets (1936), T. S. Eliot
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